Triphenylphosphine → 1-(3-Bromopropyl)-1,2,3,4-tetrahydronaphthalene

HRID 1093495Notes

Reaction equation

HRID 1093495 reaction equation
O[CH2:2][CH2:3][CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>C(Cl)Cl>[Br:34][CH2:2][CH2:3][CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 57242163HCID 57242163, compound

Product 1

HCID 103999951-(3-Bromopropyl)-1,2,3,4-tetrahydronaphthaleneYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 94-1 (140 mg) was dissolved in methylene chloride (10 ml), triphenylphosphine (212 mg) and N-bromosuccinimide (144 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr, and at room temperature 16 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (50 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography to give the object product (190 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. customat room temperature
  4. custom16 hr
  5. washThe reaction mixture was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. additionDiethyl ether (50 ml) was added
  9. filtrationthe precipitated triphenylphosphine oxide was filtered off
  10. concentrationThe concentrate of the filtrate
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-03abb45384e247e38a49a492c7603921
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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